Aniline → 3-Bromo-N-phenyl-1-(phenylsulfonyl)-1H-pyrrole-2-carboxamide

Beteiligte Stoffe

Reaktionsschritte

In a three-necked round-bottom flask aniline (1.57 mL, 17.20 mmol) was dissolved in 80 mL of toluene under inert atmosphere. To this solution was added trimethyl aluminium (7.82 mL, 15.64 mmol) and the mixture was stirred at room temperature during 10 min. Afterwards, a solution of methyl 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate (2.0 g, 5.81 mmol) in 20 mL of toluene was added and the reaction mixture was heated at 80° C. for 3 h. Next, the mixture was allowed to cool to room temperature and 20-30 mL of water and a 0.5M aqueous solution of disodium tartrate dihydrate were added to hydrolize unreacted trimethyl aluminium. After stirring for a while, the two layers were separated and the aqueous phase was extracted with ethyl acetate. The organic mixture was washed with the same 0.5M aqueous solution of disodium tartrate dihydrate (200 mL), water and brine, dried and concentrated in vacuum to afford 2.7 g of a residue that was used in the following step without further purification.

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